WO2003011979A1 - Novel formazan reactive dyes - Google Patents
Novel formazan reactive dyes Download PDFInfo
- Publication number
- WO2003011979A1 WO2003011979A1 PCT/IB2002/002986 IB0202986W WO03011979A1 WO 2003011979 A1 WO2003011979 A1 WO 2003011979A1 IB 0202986 W IB0202986 W IB 0202986W WO 03011979 A1 WO03011979 A1 WO 03011979A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- compounds
- parts
- dyeing
- independently
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/20—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a pyrimidine ring
- C09B62/24—Azo dyes
- C09B62/242—Dyes containing in the molecule at least one azo group and at least one other chromophore group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/04—Nickel compounds
Definitions
- This invention relates to novel fibre-reactive formazan dyes of the formula (I):
- X and Y are independently halogen atoms, m, n, o, r, s and t are independently 0, 1 or 2, u is 0 or 1, v is I or 2, subject to the proviso that the sum total of u and v is always less than 3,
- X and Y are each fluorine, o is 0 or 1 , r, s and t are each 0 and both m and n are I or 2.
- the compounds of the formula I and mixtures thereof are reactive dyes; they are useful for dyeing or printing hydroxyl-containing or nitrogenous organic substrates and for use in inkjet printing inks for printing paper and optionally pretreated substrates.
- Preferred substrates include leather and fibre materials comprising natural or synthetic polyamides and especially natural or regenerated cellulose, such as cotton, filament viscose or staple viscose.
- the most preferred substrate is textile material comprising cotton.
- the compounds of the formula (I) can be used in dyeing liquors or print pastes according to any dyeing or printing process customary for reactive dyes. Preference is given to dyeing by an exhaust process employing a temperature interval of 30-60°C and preferably 50-60°C.
- This invention also provides the synthesis of the novel compounds.
- This invention accordingly further provides a process for dyeing or printing hydroxyl- containing or nitrogenous organic substrates, by dyeing or printing with the above- defined compounds, their salts or mixtures thereof.
- the present invention further provides a hydroxyl-containing or nitrogenous organic substrate which has been dyed or printed as per the above-described dyeing or printing process.
- the present invention yet further provides substrates, especially cellulose, polyamides and animal fibres, preferably cotton, which have been dyed or printed with such compounds.
- paper and optionally pretreated substrates which contain cellulose, polyamides or animal fibres and have been printed with inkjet printing inks which contain such compounds, their salts or mixtures.
- the pH of the reaction mixture is maintained between 6 and 8 by metered addition of sodium carbonate.
- Alkaline hydrolysis of the methylene group and salting out with sodium chloride leave a moist presscake which contains 65 parts of the amino formazan system of the formula Id
- the presscake thus obtained is slurried up in 500 parts of water and heated to 50°C, at which point 14 parts of 2,4,6-trifluoropyrimidine are added over 10 hours. During the addition, the pH is maintained at about 7 using sodium carbonate. The end of the reaction is followed by salting out and filtration. This provides 60 parts of a compound of the formula Ie
- Example 1 The synthesis of Example 1 is repeated, except that the compound 1 b is replaced by the compound of the formula 2b
- a dyebath containing 0.3 part of the dye of Example 1 and 15 parts of Glauber salt (calcined) in 300 parts of demineralized water is entered with 10 parts of cotton fabric (bleached) at 40°C. After 30 minutes at 40°C, a total of 6 parts of sodium carbonate (calcined) are added at intervals of 10 minutes in portions of 0.2, 0.6, 1.2 and lastly 4 parts while the temperature is maintained at 40°C. Dyeing is then continued at 40°C for one hour. The dyed material is subsequently rinsed in running cold water and then for 3 minutes in running hot water. The dyeing is washed off at the boil in 500 parts of demineralized water in the presence of 0.25 part of Marseilles soap for 15 minutes.
- the fabric After rinsing in running water (3 minutes hot) the fabric is centrifuged and dried in a drying cabinet at about 70°C. This provides a green cotton dyeing having good fastnesses, which exhibits good light and wetfastnesses in particular and is stable to oxidative influences.
- a dyebath containing 10 parts of Glauber salt (calcined) in 300 parts of demineralized water is entered with 10 parts of cotton material (bleached).
- the bath is heated to 40°C in the course of 10 minutes before 0.5 part of the dye of Example 1 is added.
- 3 parts of sodium carbonate (calcined) are added before dyeing is continued at 40°C for a further 45 minutes.
- the dyed material is rinsed with running cold water and then with hot water and washed off at the boil similarly to prescription A. Rinsing and drying leaves a green cotton dyeing which has the properties recited for prescription A.
- Example 2 - 4 or dye mixtures of Examples 1 - 4 can likewise be used for dyeing similarly to prescriptions A and B.
- the dyeings obtained possess good fastness properties.
- the printed material is steamed at 102 - 104°C for 4 - 8 minutes and then rinsed cold and hot.
- the fixed cotton material is subsequently washed off at the boil (similarly to prescription A) and dried.
- the bluish green print obtained exhibits good general fastnesses.
- Examples 2 - 4 or dye mixtures of Examples 1- 4 can likewise be used for printing cotton similarly to prescription C. Bluish green prints having good fastness properties are obtained in all cases.
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BRPI0211487-9A BR0211487B1 (en) | 2001-07-31 | 2002-07-29 | fiber-reactive formazan dye compounds and their use. |
JP2003517159A JP2005523341A (en) | 2001-07-31 | 2002-07-29 | New formazan reactive dye |
EP02749227A EP1414911A1 (en) | 2001-07-31 | 2002-07-29 | Novel formazan reactive dyes |
KR10-2004-7001374A KR20040019083A (en) | 2001-07-31 | 2002-07-29 | Novel formazan reactive dyes |
US10/484,564 US7015314B2 (en) | 2001-07-31 | 2002-07-29 | Formazan reactive dyes |
MXPA04000878A MXPA04000878A (en) | 2001-07-31 | 2002-07-29 | Novel formazan reactive dyes. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1423/01 | 2001-07-31 | ||
CH14232001 | 2001-07-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2003011979A1 true WO2003011979A1 (en) | 2003-02-13 |
Family
ID=4565465
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/IB2002/002986 WO2003011979A1 (en) | 2001-07-31 | 2002-07-29 | Novel formazan reactive dyes |
Country Status (10)
Country | Link |
---|---|
US (1) | US7015314B2 (en) |
EP (1) | EP1414911A1 (en) |
JP (1) | JP2005523341A (en) |
KR (1) | KR20040019083A (en) |
CN (1) | CN1289610C (en) |
BR (1) | BR0211487B1 (en) |
MX (1) | MXPA04000878A (en) |
TW (1) | TW593566B (en) |
WO (1) | WO2003011979A1 (en) |
ZA (1) | ZA200309214B (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100482248C (en) * | 2004-02-11 | 2009-04-29 | 吴芳 | Application of 'Kidney Benefiting Injection' in the process for preparing medicine to treat diabetic nephropathy |
CN100482249C (en) * | 2004-02-11 | 2009-04-29 | 吴芳 | Application of 'Kidney Benefiting Injection' in the process for preparing medicine to treat nephrotic syndrome |
US11441830B2 (en) | 2018-12-26 | 2022-09-13 | Rebound Technologies, Inc. | Solid production systems, devices, and methods utilizing oleophilic surfaces |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2000893A6 (en) * | 1966-04-22 | 1969-09-19 | Geigy Ag J R | Dyes of the formazan series, their preparation and applications. |
EP0526792A2 (en) * | 1991-08-03 | 1993-02-10 | Bayer Ag | Reactive dyes containing a fluoropyrimidine group |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4241918A1 (en) | 1991-12-20 | 1993-06-24 | Sandoz Ag | |
CH690649A5 (en) | 1995-06-07 | 2000-11-30 | Clariant Finance Bvi Ltd | Phthalocyanine reactive dyes for fibers. |
-
2002
- 2002-07-29 JP JP2003517159A patent/JP2005523341A/en active Pending
- 2002-07-29 WO PCT/IB2002/002986 patent/WO2003011979A1/en active Application Filing
- 2002-07-29 CN CNB028150023A patent/CN1289610C/en not_active Expired - Fee Related
- 2002-07-29 MX MXPA04000878A patent/MXPA04000878A/en active IP Right Grant
- 2002-07-29 BR BRPI0211487-9A patent/BR0211487B1/en not_active IP Right Cessation
- 2002-07-29 US US10/484,564 patent/US7015314B2/en not_active Expired - Fee Related
- 2002-07-29 EP EP02749227A patent/EP1414911A1/en not_active Withdrawn
- 2002-07-29 TW TW091116879A patent/TW593566B/en not_active IP Right Cessation
- 2002-07-29 KR KR10-2004-7001374A patent/KR20040019083A/en not_active Application Discontinuation
-
2003
- 2003-11-26 ZA ZA200309214A patent/ZA200309214B/en unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2000893A6 (en) * | 1966-04-22 | 1969-09-19 | Geigy Ag J R | Dyes of the formazan series, their preparation and applications. |
EP0526792A2 (en) * | 1991-08-03 | 1993-02-10 | Bayer Ag | Reactive dyes containing a fluoropyrimidine group |
Non-Patent Citations (1)
Title |
---|
LEHR F: "SYNTHESIS AND APPLICATION OF REACTIVE DYES WITH HETEROCYCLIC REACTIVE SYSTEMS", DYES AND PIGMENTS, ELSEVIER APPLIED SCIENCE PUBLISHERS. BARKING, GB, vol. 14, no. 4, 1990, pages 239 - 263, XP000176926, ISSN: 0143-7208 * |
Also Published As
Publication number | Publication date |
---|---|
US20040167321A1 (en) | 2004-08-26 |
US7015314B2 (en) | 2006-03-21 |
BR0211487B1 (en) | 2012-11-27 |
CN1289610C (en) | 2006-12-13 |
CN1537148A (en) | 2004-10-13 |
MXPA04000878A (en) | 2004-06-03 |
KR20040019083A (en) | 2004-03-04 |
ZA200309214B (en) | 2004-11-26 |
TW593566B (en) | 2004-06-21 |
BR0211487A (en) | 2004-08-17 |
EP1414911A1 (en) | 2004-05-06 |
JP2005523341A (en) | 2005-08-04 |
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